1 cup semisweet chocolate chips, melted, cooled slightly
1 teaspoon vanilla extract
Heat oven to 350 degrees F. Spray two 9-inch cake pans with cooking spray.
In a medium mixing bowl, sift together flour, cocoa powder, baking powder, baking soda and salt. In a large mixing bowl, whisk together eggs, oil and sugar until well combined. Gradually whisk in flour mixture, alternating with 3/4 cup Cheerwine. Divide batter into cake pans. Bake 12-14 minutes or until well risen, and a toothpick inserted into cake comes out with moist crumbs attached. Cool 12 minutes before running a knife around outside pan edges and inverting cakes out onto wire racks to cool completely.
Boil the remaining Cheerwine in a small saucepan until reduced by half (should be a thicker syrup). Brush cakes with syrup to make them nice and moist. If you have any remaining syrup, you can add it to the frosting for extra flavor.
To make the frosting, whisk together sugar, flour and milk in a small saucepan. Bring to a boil, stirring constantly, until mixture thickens up. Transfer mixture to a large mixing bowl and chill in the refrigerator until room temperature. Add butter to bowl, and mix, using a mixer on medium speed, until well combined. Beat in melted chocolate and vanilla until well combined and fluffy. Frost cake. Decorate with cherries, if desired.